Therapeutical compound.



No Drawing.

" STATES" PATENT OFFICE.

wrnnnnmnrnunnz ANDYW'ALTER mm, or'nnnmnnn, Gnrmnmr, AssIGNons' 'ro rnnnnnrannrxnn vonm. ramnn, BAYER- a 00., OF'ELBERFE'LD, GERMANY, A

conrom'r-rou lot GERMANY.

rHEnArnU'rIcAL' COMPOUND.

To all whom. it may concern:

Be it known that we, WILHELM HInMENz and WALTER Knorr, doctors of philosophy, chemists, citizens of the German Empire, residing at Elberfeld, Germany,'have invented new and useful Improvements in TherapeuticalCompounds, of which the following is a specification. 1

The present application which is in part a continuationof application from our application Ser. No. 632424, filed June 10,1911 concerns the production of the hitherto unknown esters of mono and di-iodocinnamic acid of the formula -OG H,,-OCH,,, etc, which are stable pure iodin preparations. I They give oif iodin inthe-organism and have proved to be valuable remedies in medicine, especially for treatment of venereal diseases, an average dose being from 2,3 grams. Clinical experience has shown that the symptoms of iodism are very rarely observed in their ad-- ministration.

The process for producing the newesters consists in converting, the iodocinnamic acids, such as diiodocinnamic acid, beta iodocinnamic acid, .etcL, into the chlorids'" and heating the 'chlorids of the iodo or diiodocinnamic'acids with alcohols orin introducing iodin into the esters of the phenylpropiolic acids.

Ournew preparations are crystalliz able compounds. They are j insoluble in water and are decomposed by treatment with a hot alcoholic 'solution'of caustic potash.

solution. It can be recrystallizedfrom .al-

c,,H, .cI=oI cooc,H, isthen precipitated with water from this Specification of-Le'tters Patent.

rier of iodin.

Patented Mar. 18,1913.

Application filed August 28, 1 911. Serial No. 646,875. r

cohol, melts at 63 C. and is easilf"; soluble in ether but diflicultly in water. Glacial acetic acid can be replaced by other solvents e, g. carbon-disulfite, carbon-tetrachlorid, etc. Other derivatives can also be iodized in the same manner with or without a car- Example 2: 12 parts of beta-iodocinnamic acid (Michael, Ber. d. Deutschen Chem. G68.

34, 1901, page-3659) are heated with. 10

parts of PC1 in 50 parts of carbon v tetrachlorid for three hours to 50- C. Carbon-tetrachlorid and P001, are removedtin vacuo and the residue is dissolved in 25 parts of carbon-tetrachlorid and mixed with 5.5 parts of guaiacol in 25 arts'of carbontetrachlorid. The mixture is boiled for six hours, until the evolution of hydrochloric acid ceases. Guaiacol ester separates from the cooled mixture in the shape of yellow crystals showing the melting point: 131 C.

This substance is insoluble in water and difficulty soluble in ligroin, carbon-tetra chlorid and petrol ether. 'It is rather soluble in ether, alcohol and benzene when heated and easily soluble in acetone and chloro- .form. The ethyl ester of paranitro-diiodocinnamic acid crystallizes in the shape of yellow prismatic crystals melting at 89- C.

We claim 1. .As new products esters of lodocinnamic acids, which are practically insoluble in water, being decomposed by treatment with hot alcoholic potash solutioninto potassiumiodid and phenylpropi'olic acid.

2. As new products alkyl esters of iodoci'nnamic acids, which are practically insoluble in water, being decomposed by treatment with hot alcoholic potash solut1on into potassium iodid and phenylpropiolic acid.

3. As new products esters of'di-iodo-cim namic acids, which are practically insoluble. in water, bein decomposed by treat ment with hot alco olic solution into .potas;

sium iodid and phenylpropiolic acid.

, 4. As new products alkyl esters of diiodocinnamic acids, which are practically insoluble in water, being decomposed by .treatment'with hot alcoholic solution into potassium iodid and phenylpropiolic acid.

5. The ethyl ester of diiodocinnamic acid set our hands the presence of two subwhich crystallizes from alcohol in the shzipe scribing witnesses.

of hexagonalic plates melting at 63 C. be- WILHELM HIEMENZ. [1 5.] in easily soluble in ether, but soluble with WALTER KROPP. [L. 15.] di culty in water, substantially as de- Witnesses:

scribed. L. NUFER,

In testimony whereof We have hereunto ALBERT F. NUFER. 

